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Hindawi Publishing Corporation

International Journal of Polymer Science


Volume 2012, Article ID 907049, 8 pages
doi:10.1155/2012/907049

Research Article
Physical Properties of Soy-Phosphate Polyol-Based Rigid
Polyurethane Foams
Hongyu Fan,1 Ali Tekeei,2 Galen J. Suppes,2 and Fu-Hung Hsieh1
1 Department
2 Department

of Biological Engineering, University of Missouri-Columbia, 248 AE Building, Columbia, MO 65211, USA


of Chemical Engineering, University of Missouri-Columbia, W2033 Laerre Hall, Columbia, MO 65211, USA

Correspondence should be addressed to Fu-Hung Hsieh, hsiehf@missouri.edu


Received 28 October 2011; Accepted 21 December 2011
Academic Editor: Jose Ramon Leiza
Copyright 2012 Hongyu Fan et al. This is an open access article distributed under the Creative Commons Attribution License,
which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Water-blown rigid polyurethane (PU) foams were made from 050% soy-phosphate polyol (SPP) and 24% water as the blowing
agent. The mechanical and thermal properties of these SPP-based PU foams (SPP PU foams) were investigated. SPP PU foams with
higher water content had greater volume, lower density, and compressive strength. SPP PU foams with 3% water content and 20%
SPP had the lowest thermal conductivity. The thermal conductivity of SPP PU foams decreased and then increased with increasing
SPP percentage, resulting from the combined eects of thermal properties of the gas and solid polymer phases. Higher isocyanate
density led to higher compressive strength. At the same isocyanate index, the compressive strength of some 20% SPP foams was
close or similar to the control foams made from VORANOL 490.

1. Introduction
Polyurethanes (PU) are important chemical products and
over three quarters of the PU are consumed in the form of
foams globally [1]. Isocyanates and polyols are two major
components in polyurethane (PU) production, and they
both rely on petroleum as feedstocks [24]. In recent years,
various factors motivate foam researchers to investigate potential and renewable resources as feedstocks of polyols.
United States is a major producer of soybean oils and the
price of soybean oil is forecasted to be relatively stable, ranging near $9.209.25 per bushel in the next decade [5]. Besides, refined soybean oils contain more than 99% triglycerides with active sites amenable to chemical reactions [6].
Therefore, soybean oil (SBO) is one of the most promising
biobased resources as a feedstock of polyols for PU manufacture. Several synthetic approaches have been reported to
introduce hydroxyl groups to the triglycerides: (1) hydroformylation followed by hydrogenation [7], (2) epoxidation
followed by oxirane opening [810], (3) ozonolysis followed
by hydrogenation [11, 12], and (4) microbial conversion
[13]. It has been reported that flexible and rigid PU foams
could be made with a mixture of petroleum polyol and soybean oil-based polyols [1416].

Soy-phosphate polyol (SPP) is made from the SBO-derived epoxides with the presence of phosphate acid as catalyst by acidolysis reaction. Normally, the acidolysis reaction
is carried out by mixing SBO-derived epoxides, o-phosphate
acid (o-H3 PO4 ), water, and polar solvents, and the oligomerization occurs instantly to produce clear, viscous, homogeneous SPP with a low acid value and high average functionality.
In this reaction, SBO-derived epoxide is able to directly react
with water to form diols because of their high reactivity
through cleavage of the oxirane ring [17]. Phosphoric acid
not only catalyzes ring-opening reaction but also is chemically involved to become part of the polyol [18, 19]. Guo et al.
[19, 20] prepared SPP by using water and a significant
amount of polar solvents to obtain high hydroxyl functionality while keeping the final acid value low.
The distilled water, acting as blowing agent, reacts with
isocyanate to generate carbon dioxide, which blows the reactant mixture to form a cellular structure. It is an important
parameter that influences the properties and performance of
rigid PU foams. By varying the amount of distilled water,
Thirumal et al. [21] studied the eect of foam density on the
properties of rigid PU foams made from a petroleum polyol.
They found that the strength properties increase with the increase in density of the foams and their relationship can

2
be roughly depicted by the Power law [22, 23]. Campanella
et al. [24] analyzed the eect of foaming variables, such as
water content, polyol reactivity, catalyst, surfactant, and isocyanate, on the structure and properties of soybean oil-based
PU foams. Water was used as a reactive blowing agent to
produce CO2 with isocyanate. They found that an increase in
the water content produced more CO2 and resulted in a larger foam volume as well as lower foam density. Also, the foam
morphology was influenced by the water content. An increase in the water content produced rigid PU foams with
thinner foam cell walls and larger foam cells, changing the
density and morphology of the foams.
Isocyanate, which is derived from petroleum, is another
critical component in PU production. Its amount (or the isocyanate index) and property greatly aected the performance
of PU foams [25, 26]. Guo et al. [27] investigated eect of
isocyanate index (ranging from 110 to 130) on compressive
strength of rigid PU foams made from soybean-oil-based
polyol. They found that compressive strength of soy-polyolbased foams varied proportionally with isocyanate index
when isocyanate index was over 100, indicating that the
mechanical property of rigid foams could be modified by
altering the amount of isocyanate used in the foaming formulation. They concluded that excess isocyanate used in the
foam formulation gave rise to a more rigid structure in rigid
PU foams because of the more complete conversion of OH
groups in polyols and the reaction of isocyanate with moisture in the air. Tu et al. [28] studied the physical properties of
water-blown rigid PU foams containing epoxidized soybean
oil with an isocyanate index ranging from 50 to 110. They
reported that the foam density decreased when the isocyanate index decreased to 60, but a sharp increase in density
occurred at isocyanate index 50 due to foam shrinkage. Also,
the compressive strength decreased with decreasing isocyanate index. Decreasing the isocyanate index would reduce
isocyanate and meanwhile increase the bio-based content in
PU formulations. In this study, the objective was to investigate the eect water (blowing agent) content and isocyanate
index on the physical properties of SPP PU foams.

2. Materials and Methods


2.1. Materials. The petroleum-based polyol and isocyanate
used in this study were VORANOL 490 and PAPI 27, respectively. Both were obtained from Dow Chemical Co. (Midland, MI). Their specifications are shown in Tables 1 and
2, respectively. Soy-phosphate polyol (SPP) was prepared at
the University of Missouri and its specification is shown
in Table 3. It was made by an acidolysis reaction as shown
in Figure 1 [18]. Full-epoxidized soybean oil (7.0% oxirane,
Vikoflex 7170, Arkema, King of Prussia, PA) was reacted with
1.5% o-H3 PO4 (85% aqueous from Fisher Scientific), added
drop wise in a beaker under vigorous mechanical stirring at
room temperature for 5 min [18]. Dimethylcyclohexylamine
and pentamethyldiethylenetriamine were used as catalysts.
They were from Sigma-Aldrich (St. Louis, MO). Dabco DC
5357 (Air Products and Chemicals, Allentown, PA) was used
as a surfactant.

International Journal of Polymer Science


Table 1: Specifications of polymeric isocyanate PAPI 27 [29].
Properties
Density, g/mL at 25 C
Average molecular weight
Functionality
NCO content by weight, %
Viscosity, cps at 25 C
Acidity, %
Vapor pressure, mm Hg at 25 C
Decomposition point C

Values
1.23
340
2.7
31.4
150220
0.017
<105
230

Table 2: Specifications of VORANOL 490 [30].


Properties
Density, g/cm3
Hydroxyl number, mg KOH/g
Functionality
Average molecular weight, g
Flash point, 0 C
Water content, %
Viscosity, mPa.s (at 25 C)

Values
1.11
484.8
4.3
460
31.4
0.007
6180

Table 3: Specifications of soy-phosphate polyol [18].


Properties
Hydroxyl number, mg KOH/g
Viscosity, mPas (at 25 C)
Acid number

Values
240
3946.8
0.5

2.2. Experimental Design and Foaming Formulations. This


experiment consisted of two stages. In the first stage, the effect of water content (2, 3, and 4%) with dierent soy-phosphate polyol (SPP) percentages (0, 10, 20, 30, 40, and 50%)
on the properties of rigid PU foams were studied. Table 4
shows the foaming formulations for rigid SPP-based polyurethane foams (SPP PU foams). Based on the results obtained
from the first stage, the water content was fixed at 3% at the
second stage to study the eect of isocyanate index and SPP
percentage on the properties of SPP PU foams. The formulations are shown in Table 5.
2.3. Foam Preparation. The water-blown rigid polyurethane
foams were made through one-shot and free-rising method.
A total of 100 g of VORANOL 490 and soy-polyol mixture
were weighed in a plastic container. Other B-side components such as water, catalysts, and surfactant were added successively and all B-side materials were mixed with an electric
mixer at 3450 rpm for 2 min. The mixture was allowed to
degas for 2 min. Thereafter, preweighed isocyanate (A-side
material) was added rapidly and mixed at the same speed for
10 s. Then, the reacting mixture was poured quickly into a
wooden mold (11.4 11.4 21.6 cm) with aluminum lining
and the foam was allowed to free-rise and set at ambient

International Journal of Polymer Science

3
OH

O
O

OH
O

H2 O
+

HO

H3 PO4

H+

OH

O
P

O
O H

O
O

ESBO

H
O
OH

Phosphate ester

o -Phosphoric acid

Figure 1: Schematic representation of soy-phosphate formation.


Table 4: Foaming formulation of rigid polyurethane foams with dierent soy-phosphate polyol percentages.
Ingredients
B-side materials
VORANOL 490
(petroleum-based polyol)
Soy-phosphate poyol (soybean
oil-based polyol)
Dimethylcyclohexylamine
(gelling catalyst)
Pentamethyldiethylenetriamine
(blowing catalyst)
Dabco DC 5357 (surfactant)
Distilled water (blowing agent)
A-side material
Isocyanate indexb of PAPI 27

Parts by weighta
Control PU foams

SPP PU foams

100

90, 80, 70, 60, 50

10, 20, 30, 40, 50

0.84

0.84

1.26

1.26

2.5
2.0, 3.0, 4.0

2.5
2.0, 3.0, 4.0

110

110

a All

recipes and calculations are based on 100 total parts by weight of polyol, which conventionally dictates that the sum of all polyols adds up to 100 parts.
b The amount of isocyanate is based on the isocyanate index. The isocyanate index is the amount of isocyanate used relative to the theoretical equivalent
amount.

Table 5: Foaming formulation of rigid polyurethane foams with dierent isocyanate indices.
Ingredients
B-side materials
VORANOL 490
(petroleum-based polyol)
Soy-phosphate poyol (soybean
oil-based polyol)
Dimethylcyclohexylamine
(gelling catalyst)
Pentamethyldiethylenetriamine
(blowing catalyst)
Dabco DC 5357 (surfactant)
Distilled water (blowing agent)
A-side material
Isocyanate indexb of PAPI 27

Parts by weighta
Control PU foams

SPP PU foams

100

80, 50

20, 50

0.84

0.84

1.26

1.26

2.5
3.0

2.5
3.0

70, 80, 90, 100, 110

70, 80, 90, 100, 110

a All

recipes and calculations are based on 100 total parts by weight of polyol, which conventionally dictates that the sum of all polyols adds up to 100 parts.
b The amount of isocyanate is based on the isocyanate index. The isocyanate index is the amount of isocyanate used relative to the theoretical equivalent
amount.

conditions (23 C) for 7 days before measurement except


thermal conductivity which was conducted within 2448 h.
2.4. Foam Property Measurements. The apparent density of
foam samples was measured according to the American Society of Testing Materials (ASTM) designation: D1622-08

(2008) [31]. The apparent thermal conductivity of rigid


foams (20 20 2.5 cm) was determined according to ASTM
designation: C518-10 [32] and was tested by a Fox 200
heat flow meter instrument (LaserComp, Wakefield, MA),
after foam curing at room temperature (25 C) for 2448 h.
The compressive strength was determined according to
ASTM Designation: D1621-10 [33] by a TA.HDi Texture

3. Results and Discussion

70
65

Density (kg/m3 )

Analyzer (Texture Technologies Corp., Scarsdale, NY). The


compressive strength was also tested after foam was stored
seven days at room temperature. The dimension of the specimen in both density and compressive strength was 6.35
6.353.81 cm. Five specimens per sample were measured and
the average was reported.

International Journal of Polymer Science

3.1.2. Closed Cell Percentage and Thermal Conductivity. The


eect of SPP percentage on the closed cell percentage and
thermal conductivity of rigid PU foams with dierent water
contents was shown in Figures 3 and 4, respectively. In the
foaming process, water reacted with isocyanate to produce
carbon dioxide, which expanded the gelling polymer creating
many small cells in the foam. At the same water content, the
closed cell percentage of PU foams decreased with increasing
SPP percentage. The functional hydroxyl groups of SPP were
secondary, while in VORANOL 490 they were primary [38,
39]. It is known that the primary hydroxyl groups react three
times faster than secondary groups with isocyanate [37, 40].
The lower reactivity between the SPP and isocyanate might
have diminished the foam cell strength and meanwhile given

55
50
45

3.1. Eect of Water Content

40
35

10

20

30

40

50

SPP (%)
2% H2 O
3% H2 O
4% H2 O

Figure 2: Eect of SPP percentage on density of rigid PU foams


with dierent water contents.

100

90
Closed cell (%)

3.1.1. Density. Figure 2 shows the eect of soy-phosphate


polyol (SPP) percentage on the density of rigid PU foams
with dierent water contents. At 2% water content, the density of PU foams decreased slightly with increasing SPP percentage. Because SPP has a lower hydroxyl number (OH
number of 240) than the petroleum-based polyol, VORANOL 490 (OH number of 490), a higher percentage of SPP
would require less isocyanate in the foam formulation. Furthermore, when the water content was fixed at 2%, the same
amount of carbon dioxide was generated in the PU foams.
Thus, all foam volumes remained essentially the same and
the density of foams decreased slightly with an increase in
SPP percentage. However, at 3% water content, the density
of foams did not change significantly with increasing SPP
percentage. In principle, higher water content in the foaming
formulation process generated more volume or amount of
carbon dioxide gas [34]. More carbon dioxide forced the cell
walls of the foams to become thinner, causing a weaker threedimensional network, which led to decreased closed cell
percentage (Figure 3) [3537]. Even though less isocyanate
was present to take part in foaming with increasing SPP percentage, the foam volume still decreased due to increase in
the open cell percentage. The eects of both decreasing
amount of isocyanate and foam volume caused the density to
remain more or less the same. At 4% water content, the density of foams did not change significantly except the foam
with 50% SPP replacement. This was caused by the same reason as 3% water content, which was discussed above. When
SPP replacement reached 50%, the closed cell content was
only 60% (Figure 3) resulting in a much lower volume
compared to other replacements. Therefore, the foam with
50% SPP replacement displayed a slightly higher density.

60

80

70

60

50
0

10

20
30
SPP replacement (%)

40

50

2% H2 O
3% H2 O
4% H2 O

Figure 3: Eect of SPP percentage on closed cell percentage of rigid


PU foams with dierent water contents.

rise to a weaker three-dimensional polymer network of cell


walls to hold the pressure of carbon dioxide trapped in the
cells. Therefore, with an increase of SPP percentage, the closed cell percentage in PU foams decreased.
The closed cell percentage decreased with increase in the
water content. This was because at a higher water content,
more carbon dioxide was generated leading to a larger foam
volume and thinner cell walls. Thinner cell walls and higher
gas volume might have weakened foam cell walls resulting in
a lower closed cell percentage.
In Figure 4, at 2 to 4% water content, the thermal conductivity decreased from 0 to 20 or 30% SPP percentage and
then increased. The thermal conductivity was mainly aected

International Journal of Polymer Science

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700
650

0.031

Compressive strength (kPa)

Thermal conductivity (W/mk)

0.032

0.03
0.029
0.028
0.027
0.026

600
550
500
450
400
350
300
250
200

0.025
0

10

20

30

40

50

10

20

2% H2 O
3% H2 O
4% H2 O

30

40

50

SPP (%)

SPP (%)
2% H2 O
3% H2 O
4% H2 O

Figure 4: Eect of SPP percentage on thermal conductivity of rigid


PU foams with dierent water contents.

Figure 5: Eect of SPP percentage on compressive strength of rigid


PU foams with dierent water contents.

by two factors: the conduction of the polymer phase and convection of the gas trapped in the cells [37, 41]. With
increasing SPP percentage in the foam formulation process,
less isocyanate was present to participate in the polymerization leading to less polymer phase. Therefore, the thermal
conductivity was reduced when increasing the SPP percentage from 0 to 20 or 30%. On the other hand, the amount
of carbon dioxide trapped in the foams decreased with increasing SPP percentage due to lower closed cell percentage
(Figure 3). Carbon dioxide has a lower thermal conductivity
(0.0146 W/mK) than air (0.024 W/mK) at room temperature [42]. The thermal conductivity of SPP PU foams was
contributed by both polymer phase and gas phase. When the
SPP was higher than 20 or 30%, the eect of decreasing closed cells (less carbon dioxide in the foam) might have exceeded the eect of decreasing polymer phase. This led to a higher
thermal conductivity.
It is interesting to note that the thermal conductivity of
foams at 3% water content was lower than those at 2% and
followed by those at 4% at the same SPP percentage. As mentioned above, thinner cell walls (also less polymer phase) or
higher closed cell percentage contributes to a lower thermal
conductivity. Higher water content produced more gas,
larger foam volume, and, therefore, thinner cell walls in the
foam. At 4% water content, foams had the lowest closed cell
percentage but more gas volume. At 2% water content, foams
had the highest closed cell percentage but the lease amount
of carbon dioxide trapped in the cells as well as the thickest
cell wall. It appears foams at 3% water content had the lowest
thermal conductivity was due to the balanced eects from the
closed cell percentage and amount if gas trapped in the cells.

Density and the number of cross-links of polymer network


are two main factors that aect property of compressive
strength of PU foams. Higher density and/or more crosslinks give rise to a higher compressive strength [43, 44]. As
the SPP percentage increased, less isocyanate was present in
foaming. Therefore, fewer cross-links were generated by the
reaction of hydroxyl and isocyanate functional groups [15,
45]. In addition, the foam density decreased slightly as the
SPP percentage increased (Figure 2). Therefore, with increasing SPP percentage, the compressive strength decreased, due
to both decreases of cross-links and density in PU foams.
Increasing the water content from 2 to 4% reduced the
compressive strength (Figure 5). This was mainly due to the
eect of water content on the foam densityhigher density
would result in higher compressive strength. As shown in
Figure 2, the density of foams at 2% water content was higher
than at 3% and followed by at 4%. Therefore, the compressive strength of foams followed the same order.
In summary, the water content had a significant eect on
the physical properties of SPP PU foams. Higher water content generated more carbon dioxide. Therefore, foams had
larger volume, lower density, as well as lower compressive
strength. Based on the previous results, SPP rigid PU foams
with 3% water content had the best thermal conductivity,
medium density, and compressive strength. Therefore, the
eect of isocyanate index was investigated at 3% water content.

3.1.3. Compressive Strength. Figure 5 shows the eect of SPP


percentage on the compressive strength of rigid PU foams
with dierent water contents. At 2% water content, the compressive strength decreased with increasing SPP percentage.

3.2. Eect of Isocyanate Index


3.2.1. Density. Figure 6 shows the eect of isocyanate index
on the density of rigid PU foams at 20 and 50% SPP. As
shown, with the exception of 50% SPP PU foam at index 70,
foam density increased when increasing the isocyanate index.
Increasing isocyanate index raised the actual amount of isocyanate in the polymerizing reaction, thereby increasing

International Journal of Polymer Science


500

48

450
Compressive strength (kPa)

50

Denity (kg/m3 )

46
44
42
40
38

400
350
300
250
200
150
100

36

50

34
70

80

90

100

110

28

30

32

34 36 38 40 42 44
Isocyanate density (kg/m2 )

46

48

50

Isocyanate index
100% V490
20% SPP
50% SPP

100% V490
20% SPP
50% SPP

Figure 6: Eect of dierent isocyanate index on density of rigid PU


foams with dierent SPP percentages.

500

Compressive strength (kPa)

450
400
350
300
250
200
150
100
50
70

80

90
Isocyanate index

100

110

100% V490
20% SPP
50% SPP

Figure 7: Eect of dierent isocyanate index on compressive


strength of rigid PU foams with dierent SPP percentages.

the total amount of polymer network [46]. On the other


hand, the foam volume was dictated by the amount of carbon dioxide generated by the reaction of water and isocyanate. This reaction was independent of the isocyanate index
since isocyanate was not limiting when reacting with water.
Therefore, the foam volume did not change with the SPP
percentage which was also observed in the experiment. With
more isocyanate in the foam formulation (increasing isocyanate index), foam density increased.
3.2.2. Compressive Strength. Figure 7 shows the eect of different isocyanate indices on compressive strength of rigid PU

Figure 8: Results of compressive strength versus isocyanatye density.

foams at 20 and 50% SPP. Raising the isocyanate index


increased the compressive strength of foams. This was because the more the isocyanate used in the foam formulation,
more cross-links were formed from the reaction of isocyanate
and the hydroxyl groups in the polyols. In addition, foam
density increased with the isocyanate index (Figure 6). Both
increases in cross-links and density contributed to higher
compressive strength.
The compressive strength of 50% SPP foam was less than
the 20% SPP foam and both SPP foams were less than the
control (Figure 7). This might be due to the dierence in the
reactivity of isocyanate with the hydroxyl groups that were in
the petroleum polyol in the control (primary) and those in
the SPP (secondary). This might have resulted in less crosslinks when increasing the SPP percentage from 0 to 50%. In
addition, the density of control foam was also greater than
the SPP foam leading to higher compressive strength.
3.2.3.Compressive Strength versus Isocyanate Density. Figure 8
displays the results of compressive strength versus isocyanate
density of rigid PU foams. The isocyanate density was calculated by percent of isocyanate multiplying by the density of
PU foams (Table 6). As shown, at the same SPP percentage,
higher isocyanate density foams were harder or had higher
compressive strength. While the compressive strengths of
50% SPP PU foams were always inferior to those of 100%
VORANOL 490 PU foams, it is interesting to note that some
20% SPP PU foams were close or similar to control in compressive strength at the same isocyanate density.

4. Conclusion
In summary, water-blown rigid polyurethane foams were
produced by combining 0 to 50% soy-phosphate polyol
(SPP) with petroleum-based-polyol VORANOL 490 using

International Journal of Polymer Science

7
Table 6: Calculation of isocyanate density.

SPP

20%

50%

Isocyanate
index

Foam
density
(kg/m3 )

Theoretical
isocyanate
amount (g)

Actual
isocyanate
amount (g)

Isocyanate
mass fraction

110
100
90
80
70
110
100
90
80
70
110
100
90
80
70

48.29
44.25
41.97
38.5
35.77
45.62
43.40
39.65
36.88
36.39
45.40
41.87
39.36
36.98
47.18

176.62
160.57
144.50
128.45
112.40
176.62
160.57
144.50
128.45
112.40
176.62
160.57
144.50
128.45
112.40

176.62
160.57
144.50
128.45
112.40
163.73
148.85
133.97
119.08
104.20
144.40
131.28
118.15
105.02
91.88

1
1
1
1
1
0.93
0.93
0.93
0.93
0.93
0.82
0.82
0.82
0.82
0.82

24% water as the blowing agent. The results showed that


the water content significantly aected the physical properties of the final SPP PU foams, such as density, compressive
strength, and thermal conductivitylowest water content
produced foams with the least volume but the highest density
and compressive strength. The lowest thermal conductivity
was observed in SPP foams at 3% water content. Because the
hydroxyl number of SPP was lower than VORANOL 490,
compressive strength of SPP foams decreased when increasing the SPP percentage in the foaming formulation. Increasing the isocyanate index or isocyanate density raised the compressive strength of SPP foams. At the same isocyanate index,
the compressive strength of some 20% SPP foams was close
or similar to the control foams made from VORANOL 490.

Acknowledgments
The authors thank the United Soybean Board for the financial support of this study. None of the authors has conflicts
of interest with companies producing VORANOL 490, PAPI
27, Vikoflex 7170 and Dabco DC 5357.

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Isocyanate density
(kg/m3 ) = Foam
density
isocyanate mass
fraction
48.29
44.25
41.97
38.50
35.77
42.29
40.23
36.76
34.19
33.73
37.12
34.23
32.18
30.23
38.56

Compressive
strength (kPa)
461.99
424.79
376.59
347.71
324.48
379.04
346.97
313.95
253.47
197.40
264.28
232.98
167.07
147.29
84.15

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